


Bully: Slutty Edition

by InaName



Category: Bully (Video Games)
Genre: Anal Fingering, Anal Play, Anal Sex, Dubious Consent, Dubious Morality, Facials, Feminization, M/M, Oral Fixation, Oral Sex, Rimming, Spanking, Violence, Voyeurism
Language: English
Status: In-Progress
Published: 2017-09-18
Updated: 2018-01-04
Packaged: 2018-12-31 09:10:36
Rating: Explicit
Warnings: Underage
Chapters: 6
Words: 9,599
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12129201
Author URL: https://archiveofourown.org/users/InaName/pseuds/InaName
Summary: Jimmy's a loose boy in every since of the word, and now he's going to Bullworth Academy? Away from his mother's supervision?





	1. Authority Issues

Jimmy Hopkins was lying in the backseat, trying to ignore his mother’s attempt at conversation. The man she had married was twice as old as his grandfather (or at least, he looked it) and Jimmy was having none of his mother’s attempts to be nice. He was being taken to a boarding school after he had been expelled, yet again, from an expensive private school for being difficult.

Difficult was an interesting word to use, as he had actually been expelled for sucking cock in the boys restroom. He and his mom hadn’t talked about it. All she had said was she hoped he was happy embarrassing her and left the room, and later that night he heard her arguing with his new stepfather. He was now going to Bullworth Academy, where he was going to have no parental supervision. On one hand, he would miss the comfort of home. On the other, Jimmy Hopkins around a bunch of boys with little to no adult supervision? He felt his loins stir just thinking about it.

“You’ve upset your mother,” His new stepfather had said, “I have half a mind to beat you.”

“Half a mind is right, suddenly he realizes,” Jimmy replied. He had given his new stepfather a show the night before, purposefully leaving the bathroom door open as he showered. The glass on the shower door hadn’t been exactly foggy and the man had stood there for a moment longer than proper before briskly walking away. He wondered if the man would do it if they were alone, pull over on the side of the road. Jimmy bent over in the backseat, bare bottom, as his hands rained down blows on the pale globes.

“I can’t believe you, you little monster! We’ll deal with you when we get back from our honeymoon. Next year,” His mother threatened. Jimmy rolled his eyes, his mother wasn’t gonna do shit.

They pulled up to the gate of a rather posh looking school campus. Jimmy stared out the window, drinking in his new surroundings. His luggage had been sent ahead for him, and he wasn’t a fan of the uniform, but it did show off his ass nicely.

“Here we are boy, Bullworth Academy. Have fun Jimmy, I’ll think of you from our cruise ship,” His stepfather said. His mother giggled, but Jimmy knew exactly what he’d be thinking of. His stepfather was watching him intensely as his mother fiddled around in her purse, oblivious to the outside world as she searched for a tissue blotter. He stepped out of the car slowly, bending over to tie his shoe. He heard his stepfather’s breath hitch and then the car sped away.

He stood there wringing his hands and for a moment he thought about taking off. He had a couple of hundred dollars with him, he might be able to find a bus station here in town that would take him back home to Liberty City. His thoughts were interrupted by a middle aged woman saying his name.

“You must be the Hopkins boy,” Miss Danvers prattled.

“Huh? Where did you come from?” Jimmy babbled.  

“We’ve been expecting you, welcome to Bullworth Academy. I’m sure you’ll be happy here. Very happy indeed,” She said. Jimmy was hoping the same thing.

“Anyway, I can’t waste my life waiting for naughty little boys,”

 _Oh?_ Jimmy thought.

“I’ve got a MAN to make happy,”

 _Oh._ Jimmy thought, a little disappointed.

“The Headmaster is expecting you Hopkins, in his study,”

“Okay,” Jimmy said, turning around and beginning to walk away from the school.

“His study is OVER THERE boy, in the MAIN BUILDING. Don’t keep Dr. Crabblesnitch waiting, he’s a brilliant man. Brilliant, ” Miss Danvers pointed to the school. He followed her inside the gate, which squeaked to open up. He followed her up to the main building, watching the other kids mill about the schoolyard. He could see a bunch of boys in white polo shirts harassing what looked like to be a bunch of nerds. He felt a twinge of pity for those kids but kept his head down, following Miss Danvers inside.

The building was enormous, or at least that’s how it seemed to Jimmy. The entrance was completely open and there was a staircase going up both sides of the expansive walls. He followed Miss Danvers up the stairs and into the office.

“You should mind yourself boy,” Miss Danvers spoke, sneering a bit. She seemed very uncomfortable around him. He didn’t mind, he didn’t want to spend any more time around her than he had to. She sent him inside the office, and he watched her walk back down the stairs as the door to Dr. Crabblesitch’s office closed. He stood there for a moment until the man noticed him.

“Ah yes, so you must be Hopkins,” Dr. Crabblesnitch said, motioning to Jimmy to have a seat. Jimmy took one as he took in the appearance of the man in front of him. Stuffy, officious, probably in his late fifties with graying hair and a mop on his head. Was still handsome for an older man, plus he had that authority figure thing that made Jimmy want to do things that for sure would get him kicked out of school, or at least punished.

“Uh-huh,” Jimmy said, yawning and stretching in the chair, his shirt riding up his stomach a little bit.

“Not uh-huh, what?” Dr. Crabblesnitch warned. Jimmy internally rolled his eyes but played along.

“I mean, yes sir,” Jimmy responded.

“Very good,” Crabblesnitch said, opening up Jimmy’s school record.

 _Here it goes,_ Jimmy thought.

“Let me see, you’ve done a lot of naughty things haven’t you?”

 _You don’t know the half of it_.

“Vandalism, graffiti, bad language, violent conduct, disrespecting staff, and oh-” Crabblesnitch stopped reading for a moment and looked at Jimmy, possibly feigning shock, but it could have been genuine. Jimmy’s cheeks burned, and he wondered if Crabblesnitch would do the same to his other pair if he acted up.

“Sexual misconduct including performing sex acts on other boys in a school restroom, oh my my.”

“Come on, give me a break,” Jimmy said feebly. He had just arrived after all, he had to pretend he didn't enjoy being shamed for his actions, at least for now. 

“Yes, I’ve never met a boy like you Hopkins,” Crabblesnitch said, rising to his feet. Walking around his desk, he continued. Jimmy just smiled.

“Never in all my life, Hopkins you’re quite the nastiest little boy I’ve ever encountered.”

 _Wanna test that?_ Jimmy wanted to say. He was indeed, a nasty boy. He nodded his head in agreement.

“Tell me,” Crabblesnitch said, walking behind the seated Jimmy and placing his hands on the back of the chair, “Why should I waste my time with you?”

“I don’t know,” Jimmy replied. He wanted to say something more suggestive but he couldn’t get a read if Crabblesnitch was into taking advantage of nasty, naughty little boys.

“Because it’s my calling, it’s what I do! You excel in causing trouble, and I excel in FIXING little boys like you,”

“Oh you do?” Jimmy asked. He crossed his legs in a not-so-subtle manner, showing off the growing bulge in his pants to the older man.

“A-and turning them into respectable members of our community, here at the Academy,” Crabblesnitch gave Jimmy a once-over, “I’ve got a good feeling about you boy.”

“Well you know what they say, you should go with good feelings,” Jimmy said, standing up. It was a little uncomfortable to stand up with a semi-hard cock but his excitement was traipsing his inhibitions.

“I’m sure my mother has told you to do whatever is necessary to keep me in line,” Jimmy practically purred.

“Yes, she has given us permission to seek out ways to keep you out of trouble,” Crabblesnitch responded, straightening his tie.

“Well I just want you to know I’m okay with that. After all, who am I to stand between a man and his calling? You want this nasty, naughty little boy to be good don’t you?”

Crabblesnitch looked incredibly uncomfortable and Jimmy wondered if he had gone too far. Crabblesnitch didn’t speak for a moment, but when he finally did a pleasant smile spread across his face.

“Well boy, I have a feeling you and I are going to be great friends,” Crabblesnitch said, then his face grew hard.

“You keep that nose clean boy, or I shall have to clean it myself,”

“Yes sir,” Jimmy said, “I have a feeling I’ll be seeing a lot of this office though, sir. I REALLY hope you can handle that, no one else seems to be able to. This seems like a nice place. May I go?”

Crabblesnitch nodded, and Jimmy noted he seemed very flustered. Jimmy took his jacket off.

“I’ll go change into my uniform then, then I’ll look like a good boy in no time. Would you like that sir?”

“I-I don’t...just go to your dorm room Hopkins. I’m a very busy man.”

“Oh yes sir, I’m sorry sir,” Jimmy said, suddenly noticing his shoe became untied again. He turned around and bent over to tie it. He watched Dr. Crabblesnitch attempt to move past him, and Jimmy pretended to lose his balance. His bottom “accidentally” rubbing against the Headmaster’s crotch.

“Sorry! I’m so clumsy,” Jimmy cried, feigning humiliation.

“Out, Hopkins!” Dr. Crabblesnitch all but shouted. Jimmy suppressed a giggle and headed out the door of the office. Miss Danvers was returning as he exited and she sneered at him as he headed past her desk.

“Oh, you’re still here? Go change into your uniform boy,” Miss Danvers said. He nodded and quickly headed down the stairs, ignoring the gaze of the student body until he could clear his head after his encounter with the Headmaster. Or, more accurately, his failed attempt to seduce the man. This was going to be a long school year. 


	2. You Need Friends

**Summary for the Chapter:**

> Jimmy makes a friend and a few enemies.

Jimmy was heading down the stairs when the reality of the situation set in. Sure, he was thinking with his dick, and as he looked around he could certainly see some sexually repressed boys that he could have some fun with,  but there was something about this place that made him uneasy. He ran his hand over his shaved head.

_So here I am at probably the worst school in the country, whose alumni are nothing but arms dealers, serial killers, and corporate lawyers. Real scum, and that old creep thinks he can tame me? We shall see, my friend. I only give people what they have coming to them, or cumming to them._  


He headed out the door, ignoring the yelling of one of the...rather muscular and large prefects (Jimmy would find some way to get at least one of them on his side, hopefully) about changing into a uniform. As he walked to the dorm, he was struck by a few things. One, how fucking loud the members of the student body were. Jimmy wasn't in the mood to eavesdrop on other people's conversations but the bits and pieces he was hearing seemed a bit personal and he wondered why people would admit the stuff he was hearing out loud. 

He took the right turn to the boys dorm and was soon confronted by a group of boys wearing white polo shirts. They were kind of big, probably juniors and seniors. There didn't seem to be any freshmen with them. A couple of them were cute in a douchey way, which Jimmy didn't like to admit but it was his type, mostly because those guys were just as sleazy and had the same attitude towards sex that he did. Well, in a heterosexual way anyway. The blond one standing off to the side looked like he could be a lot of fun, the way he was looking at Jimmy. This redhead that was glaring at him however was going to be a problem.

"Guess what time it is?" The redhead, who Jimmy would later learn is named Wade Martin, asked. 

"I dunno, like, two o'clock?" Jimmy said, checking his watch. This guy obviously wanted a fight and Jimmy was going to be deliberately obtuse to piss him off. It worked, he could see a vein bulging out of Wade's neck.

"Time for a beatdown!" Wade shouted, and Jimmy flinched. Again. Very, very, loud.

Someone behind him shouted, "Yeah, get him, beat the new kid!"

 _Well shit_ , Jimmy thought as Wade approached. Jimmy put his fists up and the two started trading blows. Wade tried to land one on the side of his face that he blocked, and Jimmy took the moment of Wade being open to punch him in the chest. Wade grunted, falling back for a moment at the force of the blow and Jimmy socked him in the face, hard. He grabbed Wade by the shoulders and threw him to the ground. He was about to start kicking him in the ribs when he heard another voice from behind him scream. A hulking mass of a boy was standing atop the stairs in front of the door to the Boys Dorm. Jimmy gulped.

"YOU'RE DEAD NEW KID," Russell Northrop screamed, charging at Jimmy. Jimmy tried to move out of the way fast enough but he couldn't, and he was shoved backwards by Russell. He hit the ground, the wind knocked out of him when a large man appeared beside him.

"THAT'S ENOUGH. BREAK IT UP," Mr. Hattrick said, then he eyed Jimmy, "Why are you not in your uniform young man?"

"That's what I keep asking," Jimmy said, then he promptly turned around and headed up the steps to the boys dorm. He walked inside, a bit cautious, taking in his surroundings. 

A lean, muscular boy with a scar over his eyebrow stopped Jimmy on his way in. Jimmy rolled his eyes, he wanted to be alone for a minute, and he kept getting accosted by strangers.

"Hey, you're the new kid right?"

_Fuuuck off._  


" __Yeah, what's it to you?"

"Friendly, aren't you?" Gary Smith said, sizing up the other boy.

"What's your point? Back off loser," Jimmy said, brushing past him. 

"Hey, relax friend,"

_I'm not your friend but okay dude, you want some too?_  


"You're all pent up," Gary continued.

"And unless you're going to blow me, I don't see how that's any of your business," Jimmy said. Usually saying something like that would get a straight boy to leave him alone, and even most closeted gays boys. Gary eyed him warily but continued speaking.

"I'd be quiet with that or they'll put you on medication. They did to me and boy, it nearly sent me insane!"

"That's fascinating, now if you'll excuse me,"

"I said RELAX, man," Gary said, grabbing Jimmy's arm.

"Get off me dude!" Jimmy shouted. 

"You just arrived at the toughest school in the country and I'm offering to be your friend. Trust me, in a place like this you're going to need...friends," Gary said, drawing the last word out. 

"Alright, I can play nice," Jimmy said, "So how about you show me around?" 

"Sure, I'm Gary by the way. Change into your uniform and I'll meet you out here in five minutes," Gary replied. Jimmy nodded, then looked down the hallway to see if his luggage was in front of a door. It was, thankfully untouched by thieves or just curious teenage boys who want to know what their new dormmate liked to get up too. He dragged his bag inside his room. He left the door about halfway open to possibly give whomever walked by a show. He was starting to develop a real exhibitionism kink and Gary was cute, in a "too edgy 4 u needs medication" type of way. Maybe Gary would help him loosen up a bit. He closed his eyes and took a deep breath. The dorm smelled like boy alright. Not quite locker room smell (which Jimmy quite enjoyed) but he could tell boys lived here and had problems keeping this place clean. He opened his bag and took his uniform out.

He took his jacket and his shirt off first. He had opened the closet which had a mirror inside, he adjusted it to point at his door to see who was walking by. He slowly took his belt off and slowly unbuttoned them, unzipping them, then pulling them down. So far he hadn't seen Gary in the mirror, which was disappointing. A fat boy with a piss stain in the front of his pants did walk by and Jimmy decided  to scandalize him, quickly pushing his pants down. He hadn't been wearing underwear, and now he was completely nude.

"Oh-oh my god!" Pee-stain said, running past Jimmy's door. Jimmy smirked, cock twitching. He pulled a pair of briefs out of his bag, if he was going to be a schoolboy he might as well start dressing like one, and pulled them on. He finally saw Gary's face appear in the mirror as his door was pushed open.

"I was wondering what was going on in here, Algernon just ran past me like a bat out of hell," Gary mused, looking Jimmy up and down. Jimmy pulled his slacks on slowly and buttoned his shirt up, pulling the vest over it. 

"I think I traumatized the poor kid. I forgot I should probably close my door when I'm naked. With my luck I'll end up walking around the dorm naked before I even realize what I'm doing," Jimmy said. He couldn't make out the flash he saw in Gary's eyes but he was hoping it was lust. 

"Well we don't want to give everyone a show now do we?" Gary asked. Jimmy shrugged and Gary noted this reaction, and the two headed out of the dorm. 


	3. Meet Femme-Boy

**Summary for the Chapter:**

> Jimmy meets Petey and sparks fly.

Jimmy walked out of his dorm room with Gary and was brought into the common room. His eyes fixated on Gary's tight shirt, his muscles were bulging. His eyes traveled lower and observed Gary's nicely shaped ass.

_Jesus, I could eat that for days,_ Jimmy thought.

"We don't have an open bar, but we do have a soda machine," Gary said. Jimmy suddenly felt thirsty and fished for his wallet, pulling out a dollar bill and buying a Beam Cola from the machine.

He chugged it down, belched, and Gary who had walked to the bulletin board across the room made his way back over to Jimmy. Before he was able to reach him however, a scrawny boy in glasses ran past Gary, nearly knocking him off balance. Gary suddenly looked murderous.

"I'll be right back," Gary said to Jimmy, racing after the smaller boy, "Earnest you get your ass back here so I can kick it!" 

Jimmy sighed and walked back to his dorm room, collapsing on his bed. To be honest, he didn't want Gary to come back for a little while, unless Gary had planned to have a seat right on Jimmy's face for a little while. He started palming himself through his trousers, thinking about Gary's tight butt spread open in front of him. He heard a knock at his door and quickly stopped fondling himself. He looked up in surprise to see a small boy in a pink shirt standing in his door way.

"What do you want?" Jimmy asked, annoyed his alone time had been interrupted. The small boy hesitated but walked inside.

"You're the new kid right? I'm Pete, Pete Kowalski, everyone just calls me Petey though," Petey extended his hand but, in realizing what Jimmy had just been doing with his own, quickly withdrew it. Jimmy rolled his eyes. 

"Jimmy Hopkins, and don't ask how I'm doing since you just got an eyeful of it," Jimmy said, sitting up and turning around so his legs hung off the bed. 

"Right...sorry...you might want to close your door if you don't want anyone walking in on you doing...that," Pete said, turning a bit red and motioning to his door, which was wide open. Jimmy made a face.

"Oh, yeah. Sorry, habit. Not used to having anyone around to need to close it," Jimmy said, "And anyway, I've been here five minutes and people already want me dead. Even my own parents don't hate me this badly."

Jimmy rose from his bed and walked to the window, peering outside. There were some boys playing with a soccer ball outside, not the same bullies that had accosted him before. These guys were in blue letter jackets.

"Well, welcome to Bullworth. It's a dump," Pete said, crossing the room to stand next to Jimmy. Jimmy noticed that Pete kept stealing glances to his crotch, and it made him smirk. 

_Well, I might have at least one playmate here._

"Great, I've been expelled from anywhere halfway decent," Jimmy replied. He turned to face Pete and saw his cheeks were tinged with pink. He put a hand on Pete's shoulder and was going to follow that up with asking Petey if he was okay being friends with a bad boy, when a voice behind him interrupted. 

"Yeah, I've been expelled from anywhere halfway decent because I'm really bad," Gary said, clasping his hands together, mocking Jimmy. Jimmy and Pete stepped away from each other as if they had been caught doing something. Jimmy saw Gary take notice of this and Gary's lip twitched into a smile of barely concealed rage. 

"Give up the tough guy act, pal," Gary sneered. Jimmy got in his face.

"What's your problem?" Jimmy asked, more than a little annoyed. Gary had wanted to be his friend a couple of minutes ago, why was he being an asshole now? Why did he care if he was talking to Petey? Pete just stood there, his arms folded, looking uncomfortable.

"Well ADD primarily, but also life, my parents, this school, western civilization, but really honestly enough about me-OH!" Gary reached out and grabbed Pete who had been quietly trying to sneak out the room by the collar and pulling him back. He presented him to Jimmy, and Pete hung his head, defeated.

"I see you met the dorm's mascot. Ladies and gentlemen I give you femme-boy, the girliest boy in the school!" Gary's arm clapped roughly on the back of Petey's shoulder before speaking again and it made Pete jump, "Petey, don't you got some imaginary friends to go annoy?" 

"Why don't you leave me alone Gary," Pete whined, trying to get past him so he could get out the door. Jimmy didn't like this display, not one bit. Gary was being unnecessarily cruel to the smaller boy. Jimmy was about to say something when Gary cut him off.

"Look at you, ' _leave me alone Gary'. I'm really self important now that I've started puberty._  What's your problem? I'm just being nice to the new kid as he passes through Bullworth on his inevitable journey to prison," Gary said, walking around Jimmy and putting an arm around his shoulder. Jimmy pushed Gary's arm off and walked to the doorway. 

"Look I gotta unpack, would you mind getting out of here?" Jimmy asked, growing impatient with Gary's antics. 

"Now look what you've done Pete, Jimmy can't stand you already." Gary mocked, and the two walked out.

"I guess I'll show you around later," Gary called, his voice full of mock sorrow. Jimmy watched Gary walk into his dorm room. Then he grabbed Pete who looked a little lost, and more than a little upset, and pulled him back into his dorm room.

"I didn't mean you," Jimmy said gently. Pete looked uncomfortable again and Jimmy quickly shut the door. He grasped Pete's arm gently and pulled him backwards. Jimmy sat on his bed, looking up at Pete. 

"He can be a real jerk," Pete said, "Always calling me girly." 

"There's nothing wrong with being girly, Petey," Jimmy said, and Pete looked like he could die for a second. He stammered out his response, but he didn't move away from Jimmy, or try to pull his arm away that Jimmy was still touching. 

"W-what? I don't...I-I mean, people make fun of me all the time because I'm small and I like the color pink. What's wrong with the color pink? It's just a color. It compliments my skin tone-" Pete clasped his hand over his mouth and Jimmy nodded.

"Don't be embarrassed," Jimmy said then waved his hands as if clearing imaginary smoke in the air, "Judgement free zone here. Remember, you walked in on me about to jerk off earlier? And you didn't run away screaming or make fun of me." 

"I would never! I mean, everyone does it, right?" Pete asked. His cheeks were still pink and the tension between them was palpable. Jimmy could continue this conversation all night. 

"All the time for me," Jimmy said and Pete laughed, subtly inching closer. Their legs were now touching and Jimmy's arm had dropped from Pete's arm, which was now resting on his knee. 

"So you don't...think I'm weird," Pete asked, searching Jimmy's eyes for an answer. Jimmy laughed for a moment and Pete suddenly looked scared. 

"Of course I think you're weird," Pete tried to pull away from Jimmy but Jimmy grabbed his waist, keeping him still. 

"And that's okay. I'm weird too, I'm a huge horndog in fact. But in here," Jimmy motioned around his room, "You can be as weird as you want. I won't judge, I won't get mad, and I won't try to hurt you. I swear, you can be yourself around me."

"I'm not a..a tra-," Pete whispered and Jimmy's eyes widened, cutting him off.

"I didn't think you were and I don't think we're supposed to use that word anymore," Jimmy whispered. Pete nodded, looking a bit disappointed in himself.

"You're right, I shouldn't have...but you mean it? I can...be who I wanna be in here?" Pete asked, and Jimmy nodded. 

"What do you mean by that, exactly?" Jimmy asked. Pete took a deep breath and sighed. Jimmy took Pete's hands and tried his best to look supportive. This was not how he thought his day would go, but it felt like a good deed and he hadn't done enough of those lately. Plus, this one might get him laid!

"I just...feel like I have to put on this masculine facade and I-I can't...I can't really be..."

"Gay?" Jimmy finished. Pete didn't say anything but he nodded. Jimmy understood what he meant, sometimes he wanted to be a little less macho but the world didn't allow him to be. Jimmy had a straight suit of armor on with all his muscles, but Pete was pretty obviously a homo. Jimmy pulled Pete into his lap and the two just sat there like that for a moment, then Jimmy's mouth found it's way onto Pete's and they kissed. It didn't take long for the semi Jimmy was stroking earlier to come back and as their kissing grew more passionate it found its way to full mast. When Pete bumped it however, he shot off Jimmy's lap and across the room like he'd been bitten by a snake.

"Whoa, wait," Pete said, panting, "I'm not ready for that,"

Jimmy sighed and swung around, laying down on his bed, wiping sweat from his brow. 

"Okay," Jimmy said gently, "That doesn't change what I said though. You can still be yourself around me. I'll just...not assume you want to have sex with me next time, alright?" 

"O-okay," Pete stammered, "I should go now. See you later Jimmy," and just like that Pete was hurrying out of his bedroom.

"See ya," Jimmy said, and he slammed his fist down on his bed. Damn it! When was he going to get to get off today?!

 


	4. Morning Shower

**Summary for the Chapter:**

> Jimmy wakes up from a sex dream and decides to have an early shower.

_"Oh god, Jimmy," Petey moaned as he pushed a small, pink pair of panties aside to allow Jimmy access. His legs were in the air and Jimmy dived in, lapping at Pete's tight, smooth asshole greedily. Everything on Petey was pink, his lips, his panties, his nipples, his asshole, and his erection straining the small cotton fabric. Jimmy heard Gary's voice murmur in appreciation above them. Jimmy sat up, coating his fingers in lube and pushing one into Petey who moaned greedily. Gary reached down and began teasing Pete's nipples._

_"Fuck!" Petey cried as he spread his legs further open, the assault on his prostate and his nipples felt so good. Gary smirked, and Jimmy slid another finger inside Petey's tight, slick channel._

_"Looks like you're a femmeboy after all," Gary said, and Petey moaned loudly. Gary unzipped his fly, pulled his pants and his underwear down, and Petey opened his mouth. Gary's large cock slid inside and he began fucking his mouth. Pete was moaning around his cock and Gary continued to squeeze and pull on Petey's nipples. Jimmy was so hard, Pete was just opening up for everything they could give him. He was just to slip inside Pete's warmth when-_

The alarm on the beside table began to sound and Jimmy groaned, smashing the top and throwing off his covers. He was covered in sweat and his erection was straining his pants. He looked at the clock, which read six am, it was still dark outside. Jimmy had found it prudent to set his alarm a little early so he could masturbate without being bothered. He slipped out of his briefs, wrapped a towel around his waist, grabbed the rest of his toiletries exited his room, padding barefoot quietly down the hall. Opening the bathroom door, he could hear the faint sound of someone else in a shower. He hoped it was someone hot, and he could sneak a peak of them soaping themselves, or maybe jerking off as well.

Jimmy slipped inside, careful not to make a sound. The smell of soap hitting his nostrils, he made his way past the toilets and into the shower area. There were two rows of showers on each side, and most of them had curtains. Two didn't, and they were mostly avoided by younger students who were embarrassed to shower in front of anyone. Jimmy heard humming coming from one of the ones that had quite a thick curtain, but because of the lack of ventilation in the showers, the curtain was billowing and the surrounding area was fogged up. Jimmy had an idea. He hung his towel on a hook next to shower directly opposite from the one occupied by the boy Jimmy wanted so badly to spy on. And as luck would have it, this shower did not have a curtain on it. Jimmy walked inside the shower, turning it on to the hottest setting but avoiding the spray. It quickly fogged up the area and now it would be next to impossible to tell, beyond a reasonable doubt, that someone was spying on a shower. He walked back over to the other boy's shower, enjoying the feeling of the heat on his skin as he rubbed his leaking cock, and peeked inside the billowing curtain.

The blond boy who had been one of the bullies earlier was inside, and Jimmy's jaw dropped at the sight. He was muscular, a little tan but had very obvious tan lines around where his shorts had obviously been this summer. His ass pale, and Jimmy observed with satisfaction, smooth and bubbly. The boy, who Jimmy thought he had heard being called Trent earlier. He turned around and a wave of panic went through Jimmy's body, right down to the cock he was jerking. But the boys eyes were closed, and Jimmy got a good look at the boy's front as well. He wasn't chubby by any means, but his nipples were puffy and he had a little pooch on his belly. His cock was uncut, hard, and his head was peaking out of his foreskin. He was rubbing it, the skin moving back and forth on the head as his other hand rubbed upwards on his body. He started pulling on one of his nipples and moaned quietly. Jimmy wished he could latch his mouth onto one of those, sucking and making them tender while Trent jerked his cock. Then he'd get down on his knees behind him, pulling Trent's ass on his face, eating the blond boy's sweet hole while Trent rode out his orgasm.

Jimmy got another eyeful of the sweet bubble butt when Trent turned back around, pumping the body wash container he had and he began soaping his body. His hands reached around and began soaping his cheeks, and Jimmy squinted so he could see the boy’s hole. Pale pink, and winking as Trent rubbed soap over it. Jimmy was close to cumming now, rubbing his erection watching this boy play with his ass. His breath hitched when the finger slipped inside and the boy tensed. Jimmy, a split second from being caught, pulled his head back out of the curtain and quietly hurried to his own stall. He picked up his bar of soap and began lathering the bar in his hands as the curtain across from him was yanked open.

“Who’s there?!” Trent shouted, “Tell me who you were and I’ll pound you...I mean...I’ll,” Trent sounded exasperated by his fruedian slip, “Fuck,” Trent whispered. He then looked across the steam at the boy who was showering in the stall directly across from him, one that didn’t have a curtain.

“What are you doing?” Trent asked, walking towards Jimmy and hovering at the entrance of Jimmy’s open stall.

“Uh, showering,” Jimmy said, as if he had just noticed Trent. Trent stared incredulously, but couldn’t help but briefly palming his own cock at the sight of the naked boy in front of him. Jimmy too had a bubble butt, and he was short, but had muscle tone.

“Yeah, you’re showering in one of the open stalls, there are other ones with curtains you can shower in,” Trent said, but was secretly hoping Jimmy would do this all the time.

“I’m not shy,” Jimmy said simply, and bent over, soaping his legs. Trent’s eyes widened as Jimmy’s ass spread open in front of him and he could see the boy’s balls dangling. Jimmy stood back up and grabbed his shampoo.

“I’m...I’m just gonna...go dude,” Trent said, stammering.

“Okay,” Jimmy said, politely, not dismissive. Trent didn’t move, contemplating whether to ask what was burning in his mind.

“What if I stayed?” Trent asked, almost too loudly. Jimmy nodded, still not turning around.

“That would be okay too,” Jimmy replied, turning around, giving Trent a good look at his hard cock. Trent froze, he couldn’t think for a mome. Jimmy took his hand and pulled him into the shower, dropping to his knees.

“It’s okay, I’ll steer,” Jimmy moaned and wrapped his lips around Trent’s uncut tool, rubbing his own cock desperately. Finally, some relief after such a long day. Jimmy briefly wondered how long he could really go without sex before all thoughts of anything but cocks and assholes were thrown from his head when Trent grabbed his head and started fucking his face. Jimmy gagged for a moment and Trent slowed down his pace, muttering a quick apology.

Jimmy took this opportunity to pull him closer by reaching his hands around and squeezing Trent’s massive butt. It felt even better than it looked, Jimmy squeezed the round globes and slid a soapy finger between the crack. He expected Trent to push his hand away or even punch him, but Trent groaned and pushed Jimmy’s hand towards his hole. Two fingers slid inside from the momentum, and Trent moaned loudly. Jimmy slowly fingerfucked Trent while sucking his cock, he felt so warm inside. It didn’t take long for Trent to let out a high pitched moan and Jimmy pulled his mouth off the cock quickly, jerking it as Trent shot his load all over Jimmy’s face.

Trent panted in post-orgasmic bliss while Jimmy desperately stroked his own cock, groaning pitifully. Trent looked down at Jimmy, desperate to get off with cum all over his face, and started to panic. He turned away to leave when Jimmy grabbed his arm, and sat up on his knees, eye level to Trent’s ass.

“Just...wait one second okay,” Jimmy asked, and Trent relaxed. Jimmy grabbed his hips and buried his face in Trent’s ass, slurping on his hole with wanton need. Trent cried out in surprise but allowed the tongued assault on his fingered-open hole. He began to grow hard again and began to stroke again. Jimmy’s tongue crawled up his ass and Trent began pushing back on Jimmy’s face. He couldn’t believe it, but another orgasm was building inside of him, and quickly. He reached back and pushed Jimmy’s face into his ass while he stroked his cock furiously. Jimmy was moaning against his cheeks and quickly spurted all over Trent’s legs.

Trent came again moments later clenching around Jimmy’s tongue. Jimmy pulled his tongue out of Trent’s ass and the two boys just stayed in that position for a minute, panting. This was going to be a long school year, but if he kept having encounters like this, Jimmy would more than enjoy it.


	5. This is Your School

**Summary for the Chapter:**

> Gary shows Jimmy around the school and lets him know the score with the various cliques.

After Trent rinsed off and the two kissed lazily for a few moments, boys were starting to wake up and they parted ways. Jimmy walked back to his dorm room in a towel to a few appreciative glances. Gary smirked at him and Pete looked scandalized, Jimmy smiled at both of them before dropping his towel a few seconds before he entered his room, to thunderous whoops, hollers, and catcalls from the rowdier boys on the first floor. He knew they weren't being serious, just teenage boys being teenage boys, but he had already had one sexual encounter here using his tried and true methods. 

Gary peeked in his room as he pulled on his uniform. 

"Meet me in the main building before breakfast, I'll show you around this...prison," He said. Jimmy blushed for a moment, as he had indeed just had prison-style shower sex, but Gary couldn't possibly know that. 

"Sure, see you in a few," Jimmy replied, pulling on his vest. Gary nodded and pulled his head back out the door. He heard a knock a few moments later and rolled his eyes. 

"I got it Gary, meet you at-" Jimmy shouted but was cut off when Trent practically burst into his room, his eyes wide and panicking. Jimmy looked at him as if to say  _ What the hell are you doing? _

“You can’t tell ANYONE or i’ll-” Trent started but Jimmy held up a hand to silence him. 

“I wasn’t planning on it. Now, I have to be somewhere in like ten minutes so…” Jimmy motioned for Trent to leave. Trent rolled his eyes and left Jimmy’s room. Jimmy pulled his shoes and socks on, then headed out of his room. The hallways were bustling with activity, the nerds being way too loud and it was really no surprise to Jimmy when they got picked on. How hard was it to use your inside voice? 

He headed out the door quickly and up the campus to the main building, squeezing in behind a busty girl with red hair and pigtails to get inside. Gary spotted him immediately and waved him over. 

“Jimmy! Let me show you around this dump!” Gary said. Jimmy eagerly nodded and followed Gary across the main entrance, past the school store, and they stopped ten feet from the absolutely massive boy who had almost killed Jimmy the day before.

“That’s Russell’s locker,” Gary explained, “You know, the big ape who almost put you in the hospital?” 

Russell seemed to hear this and Gary swore quietly, Russell ran up to Jimmy and started menacing him. 

“Enough talk, now I SMASH YOU,” Russell growled. Jimmy couldn’t believe he was horny again after this morning’s shower shenanigans, but he suddenly really wanted to be smashed by Russell. Unfortunately, he knew that’s not what Russell meant. 

“I’m...no threat to you,” Jimmy said, waving his arms in a clear gesture of  _ Please don’t hurt me. _

“Your money, ALL OF IT!” Russell shouted. Jimmy rolled his eyes and pulled a bill he had found at the bottom of his luggage out and handed it to Russell. 

“Ha-ha, STUPID,” Russell laughed and then ran off. 

“He’s the stupid one, those are Suburban store bucks,” Jimmy said and the two boys started laughing. Gary pointed at the locker. 

“Let’s break into it and steal something, that’ll teach him a lesson.” 

Jimmy grabbed the lock and noticed it had a sticker with the combination still on the back. He looked up at Gary who was keeping a lookout. The two snickered and Jimmy quickly got the lock off the door, and they looked inside. It was surprisingly messy for school just having started a few weeks ago, and Jimmy decided to rip out the nude calendar from the door. He walked to the trash, careful not to draw any attention, and dropped it in. Gary nodded in approval, then the two headed off. 

Jimmy followed him to what looked like the girls’ restroom and saw a rather large, dumpy girl crying. He almost heaved when he saw what looked like to be little brown flakes around her mouth.

“There’s that weird girl Eunice, let’s have some fun with her!” Gary said in a stage whisper and sauntered up to Eunice. 

“Hey Eunice, what’s wrong?” Gary asked. Eunice stopped heaving for a moment and wailed. 

“He stole my chocolate!”

_ Oh thank god,  _ Jimmy thought.  _ I need to stay off that part of the internet. I’m traumatized!  _

Jimmy saw a boy taking off with an ornate box of chocolates down the hall. Gary cocked his head and Jimmy took off after him. The boy raced into the bathroom and Jimmy closed in on him, backing him into the sink. The boy, just a hair taller than Jimmy, suddenly looked terrified.

“Constantinos, really? Stealing chocolates from Eunice?” Gary called as he strolled in and the brunet boy shuddered. 

“Show him what you’re made of Jimmy,” Gary smirked. Jimmy smiled wickedly and Constantinos gulped. Jimmy punched him in the stomach as hard as he could. Constantinos lost his grip on the chocolates before he dropped to the groud and Jimmy quickly caught them before they hit the ground. Constantinos on the other hand wasn’t so lucky, he was rolling on the ground, clutching his stomach in agony. For a moment, Jimmy wondered if he had hit him too hard. 

Constantinos rolled over and vomited, a brown mess spilling out of his mouth. Jimmy grimaced and looked up at Gary.

  
“Disgusting,” Gary said plainly. Jimmy squatted down, careful to not step in the mess Constantinos just tossed up. 

“Don’t steal stuff from girls,” Jimmy lectured, “Or I’ll hurt you real badly next time. Learn to pick on people your own gender.” 

Jimmy and Gary left Constantinos moaning on the floor in his own sick and took the chocolate back to Eunice. She looked happy enough to kiss him when he brought them back. Jimmy rubbed the back of his neck shyly and the moment was awkward. Gary ended that quickly and grabbed Jimmy by the arm, pulling him into the cafeteria for breakfast. 

“Let me show you the local wildlife,” Gary said as they took a table closest to the entrance to get a good look at the student body, and Jimmy liked the student bodies he saw. 

“Here’s the deal, over there you have the nerds,” Gary gestured to a bunch of kids in green vest playing what looked like to be some kind of tabletop roleplaying game. He recognized a couple of them from the dormitory but couldn’t remember their names.

“They look pretty harmless,” Jimmy said and Gary shook his head.

“They’re actually sneaky bastards. Their turf is the library,” Gary replied, then turned his attention across the cafeteria to right in front of the line for food. A bunch of rich looking teenagers in Aquaberry sweaters greeted Jimmy’s vision. 

“Those are the preps, they’re all old moy and  _ condescending attitudes _ ,” Gary mocked. Jimmy smirked.

“Yeah, massively inbred and COMPLETELY brainless,” Jimmy responded with a giggle. 

“Very observant, Jimmy boy,” Gary said, and motioned to a little farther down the line to a bunch of boys who looked like reject from Grease. Jimmy was kind of into the leather a bit and he shifted in his seat, trying to spot which one he could probably get to fool around with him.

“Those are the greasers, they think they’re tough-”

“Or at least try to LOOK tough,” Jimmy interjected. Gary shook his head.

“I wouldn’t advise messing with them, at least not yet. They hang by the auto shop,” Gary turned his head to a table across the room and motioned to their last stop on the tour.

“And last but not least, the jocks. These guys rule the school, DEFINITELY avoid them,” Gary warned. Jimmy could see the rippling muscles and the overt displays of masculinity and suddenly wanted to use their jockstraps as oxygen masks. He shook the image from his head, he still had a full day of classes and didn’t want to get distracted. 

“Whatever, I’m not afraid of no roid monkeys,” Jimmy finally said, and Gary shrugged.

“You’ll learn, and now for the most important question,” Gary said. He scooted closer until their legs were touching and leaned into Jimmy’s ear. He looked around to make sure no one was paying attention to them and thankfully, no one was. 

“I witnessed something this morning that was very interesting,” Jimmy’s stomach dropped for a moment and he tried to jerk away but Gary grabbed his thigh to keep him in place and rubbed it  in a way Jimmy assumed to mean reassuringly. He groaned in anger and Gary let his lips brush Jimmy’s ear.

Now that you’ve seen the local wildlife and...more particularly, the...studs of Bullworth Academy who seem so ripe for the picking, which do you want to get bred by?” Gary asked, his hand moving from Jimmy’s thigh to his lower back. Jimmy’s eyes flashed in lust and he looked Gary in the eyes.

“All of them,” Jimmy said quietly. Gary’s mouth turned up into a wicked grin and Jimmy knew this year was going to be, at the very least, eventful.  


	6. Totem Pole

**Summary for the Chapter:**

> Jimmy's fantasy, and breakfast, is interrupted by some rather annoying news.

Gary scrunched up his face in confusion.  

"Huh? You zoned out for a minute there Jimmy boy. Are you on drugs? Because if they suspect that they'll test for them," 

Jimmy slowly blinked back to reality. He had been fantasizing about Gary groping him and whispering dirty things into his ear, but that didn't happen. Gary was sitting where he had been, a non-gropey distance from Jimmy. His left hand was holding a half-eaten apple and his right was fiddling with a strap on Jimmy's backpack absentmindedly. Neither was on his lower back, slipping down the back of his pants. Nor was one on his thigh, inching upwards toward his cock like he had been daydreaming about. Problem was, he wasn't sure what did actually happen.

"What? Oh, I guess I didn't get enough sleep last night," Jimmy said after a moment. Gary rolled his eyes at Jimmy like he was too stupid to pay attention. Jimmy decided to let that one slide, because he indeed wasn't paying attention. It wasn't because he was stupid though, it was because he was thinking with a different head. 

"Okay, space cadet. Anyway, like I was saying, I witnessed something very interesting this morning," Gary continued.

 _As interesting as what I did in the shower?_ Jimmy wondered. 

"I had a splitting headache this morning so I went to visit the nurse. I was half asleep so I didn't notice at first, but when I was walking back to the dorm, I saw the school gates were locked," Gary dropped the apple on his tray for effect but it was lost on Jimmy. He shifted his eyes back and forth like he was confused about what Gary meant.

"I figured they just kept the front entrance locked up tight during school hours," Jimmy replied. Gary shook his head and grabbed his own bag, pulling a notebook with the Bullworth crest on it out. He flipped to a page in the middle and opened up what looked like to be a foldout of a map. He scooted closer to Jimmy and pointed to the top of the map, and Jimmy recognized it as the front gate of the school.

"Not really, no. Usually this entrance is only locked when kids try to run away, or when we get new, angry, delinquent students," Gary gave Jimmy a pointed look and Jimmy rolled his eyes, it was too early in the morning for a fight and Jimmy wasn't keen on fighting cute boys, though he seemed to be already making a habit of it here at Bullworth.

"The school takes extra security measures for a while, at least enough time for the kid to either get it out of their system or do enough bad shit to get kicked out," Gary finished. Jimmy wracked his brain for a response. He didn't want to be stuck on campus for the entire school year. He was sure this posh, private school town had enough secrets and activities for him to explore to make being stuck here worth it. 

"So what do I do? To make them not think i'm a threat?" Jimmy asked. Gary shrugged, yawned, and stretched his arms up. He cracked his joints and Jimmy admired his jawline and the muscle tone he could see through Gary's shirt. 

"You could talk to Crabblesnitch," Gary said, then smirked, "Do some good deeds around here, help out your fellow students, and make sure he notices. Try and make a few friends that aren't complete losers like Petey, and I can see none of this appeals to you," Gary said, noting the sour look on Jimmy's face as Jimmy glared at him. 

"You're telling me I have to play nice with these assholes to get any outside privileges?" Jimmy asked bitterly. He already knew the answer, but he felt a gnawing feeling in the pit of his stomach when Gary nodded. Sure, he could be nice to people, in fact he preferred to have a wide circle of friends. Judging by how nasty the people he had already met had been to him however, he just didn't see it for himself here. He had been given dirty looks from basically every one he came across. He had already gotten into a fight, he had verbal abuse being shouted his way whenever the wrong person noticed him. 

"Unfortunately, yes. After I saw that I looked around. Because it looks like they've blocked off the entrance to the parking lot here," Gary pointed out out a 

Jimmy sighed and pushed off, standing up as the bell rang. 

"You're right, I should go talk to him," Jimmy said, turned around, and promptly tripped over the bench trying to stand up. Gary grabbed his arms to steady him as people filed out of the cafeteria, laughing at him. Jimmy's cheeks burned red.

"Maybe try and make it through your first day of classes without busting your head open, Clumsy Carl," Gary said. Jimmy wrenched himself out of Gary's grasp. 

"I'm fine, I don't need your help," Jimmy said. He grabbed his backpack and started towards the entrance. Gary followed quickly.

"Sorry _ma'am_ , didn't mean to offend your  _delicate sensibilites_ ," Gary crooned and Jimmy shoved a little too hard to be playful. 

"Where'd you go earlier anyway? When I was talking to you and you zoned out?" Gary asked. Jimmy shrugged, yet again, he was unsure about Gary's intentions towards him. Sure he had gotten Crabblesnitch hot and bothered, made out with Petey, and stuck his tongue up Trent's ass all in the span of a day but what if his luck was going to run out soon and he came onto someone who wasn't interested in him back? Could he risk ruining his reputation again? 

* * *

 

His classes flashed by in a blur. His English teacher smelled of booze and his chemistry teacher was just flat out terrifying. Steadying his nerves, he walked into the Headmaster's office and asked Miss Danvers if he was available. She gave him a look of incredulity and began to speak, but a speaker interrupted her.

"That's alright Miss Danvers, you can send the new boy in," Dr. Crabblesnitch said. Jimmy stood there for a moment.

"Miss Danvers, I hate to ask but it seems to have never gotten done before the start of the term, could you go down to the library and fetch those files we've been waiting on?"

"Oh yes sir, but I don't think she ever printed them out. I could be down there a while,"

"That's just fine, I just need them before the end of the day."

"Thank you sir, I'll try and be as quick as possible," 

"No need to rush. I should think I need a moment alone with the Hopkins boy,"

Miss Danvers gave Jimmy a hard stare that made him vaguely itchy before she stalked out of the office. Crabblesnitch's double doors creaked open and Jimmy heard a voice tell him to come inside. He looked across the room at a small mirror on Miss Danvers' desk. He looked good, good enough to seduce an older man into giving him what he wanted, right? 

Jimmy walked into the office with trepidation. Suddenly he felt nervous, what if he read the signals wrong? What if Crabblesnitch wasn't a total perv? Even if he was, was he really up for having sex with an older man? Despite fantasies of this, he had only been with boys around his age and felt a little uncomfortable with the idea of actually going through with his plan. 

"Please Hopkins, sit down," Dr. Crabblesnitch said, motioning to the chairs in front of his desk. Jimmy was silent when he sat down, unsure of how to proceed. One thing was for sure though, however he did proceed, he would need to do it with caution. 

"How are you finding Bullworth?" Dr. Crabblesnitch said, his face seemingly pleasant but mostly unreadable. Jimmy wondered if he should tell the truth. Honesty was the best policy after all, but he didn't want this to affect his ability to come and go from the school as he pleased.

"Well, to be honest, this school seems full of psychos...sir," Jimmy quickly spat out that last word in an attempt to placate the older man. Dr. Crabblesnitch nodded and stood, pushing his chair back from the desk. 

"Nonsense Hopkins, it may seem that would be the case, but it really is just the Bullworth way," Dr. Crabblesnitch said, walking around his desk and leaning against the front of it. Jimmy could practically smell Dr. Crabblesnitch's fabric softener from his seat, he probably could bury his face in his crotch without straining himself too much. 

 _My head is too close to his crotch for him to be this close to me on accident, right?_ Jimmy thought. Crabblesnitch had some nice thighs on him for an older guy. 

"What do you mean by that sir?" Jimmy asked and Crabblesnitch smiled down at him.

"It's just school spirit. Why in my day we thought nothing of... _emasculating_ the new boy," Crabblesnitch said, in a tone that sounded rather pointed. Jimmy's head was filled with flashes of images. The first of his dream of Pete, with the pink panties pulled to the side and Jimmy's fingers slipping inside of him. The second being the roles reversed, Jimmy on all fours wearing the same pair of panties Pete had. They were too small, as Jimmy was larger than Pete and hugged his bottom obscenely, and painfully tight on his genitals. He was being pinched and prodded by the boys he got in a fight with on the first day. The third flash and all the boys were gone, it was now Dr. Crabblesnitch playing with him.

"And now?" Jimmy asked. Crabblesnitch looked at him in confusion.

"Is that how you keep the boys in line now?" Jimmy elaborated. The older man's face darkened for a second before he spoke and Jimmy was nervous. 

"I mostly let the social order take care of that, provided the students in question know their place," Crabblesnitch stared down at Jimmy pointedly. Jimmy cocked his head and a smarmy smile spread across his face.

"And where is my place, _sir_?" Jimmy asked. Crabblesnitch smiled and put his hands on Jimmy's shoulders, their knees touching. 

 _Here we go_ , Jimmy thought, his cock hardening. Crabblesnitch's left hand reached up and stroked Jimmy's cheek, almost adoringly. Jimmy smiled, and Crabblesnitch's right snaked down his body to his crotch. His fingers trailed over Jimmy's hardening cock too lightly and Jimmy's legs opened up. Crabblesnitch invaded the space between Jimmy's legs with his own. The hand that was stroking Jimmy's face grabbed his jaw, and the the hand that was rubbing Jimmy's dick went down a little further and grabbed Jimmy's balls. Not rough enough that it hurt, but enough for Jimmy to stop squirming in his grasp. 

"I have you by the  _balls_ , Hopkins," Crabblesnitch all but purred. 

"Yes sir," Jimmy said, still not moving.

"


End file.
